Winchester Vacation Packages 2026 from $709

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Boston Harbor Hotel

North End

Save 100% on your flight

$709

per person

Dec 15 - Dec 17

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$727

per person

Nov 25 - Nov 28

found 7 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Raffles Boston

Back Bay

Save 100% on your flight

$1,210

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$1,399

per person

Nov 12 - Nov 15

found 17 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

The Langham, Boston

Downtown Boston

Save 100% on your flight

$809

per person

Dec 15 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

Top Winchester hotels deals

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$306 nightly

$357 total

Oct 31 - Nov 1

Total with taxes and fees

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Pool

Hot Tub

The Revolution Hotel

40 Berkeley Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$185 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.

Pet friendly

Free WiFi

Seaport Hotel Boston

1 Seaport Lane Boston MA

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$254 total

Nov 1 - Nov 2

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the steam room, bar/lounge, and concierge services.

Pool

Pet friendly

The Dagny Boston

89 Broad Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$347 nightly

$404 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A coffee shop, a communal living room, and a library are also on offer.

Pet friendly

Free WiFi

Encore Boston Harbor

1 Broadway Everett MA

$286 nightly

$320 total

Oct 28 - Oct 29

Total with taxes and fees

This luxury hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Free self parking is free for guests, and you can enjoy a meal in one of the 15 restaurants.

Spa

Parking included

Omni Parker House

60 School St Boston MA

Free Cancellation

Reserve now, pay when you stay

$298 nightly

$347 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, express check-out, and a computer station are also on offer.

Pet friendly

Free WiFi

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Winchester attractions

Winter Pond

9.0/10 (2 reviews)

Enjoy an outing to Winter Pond during your stay in Winchester. Discover the top-notch restaurants and acclaimed art scene in this vibrant area.

See properties

Frequently asked questions

How much are vacation packages to Winchester?

Treat yourself to a memorable travel experience in Winchester with a vacation package starting at just $709. Reserving your flights, hotels and tours with Travelocity is so simple. And even better, our great deals will leave you with extra cash for fun.

Where can I get the best vacation package deals for Winchester?

You can pick up awesome Winchester package deals with Travelocity. Select from as many as 400 partner airlines and 1,000,000 properties worldwide and turn your travel dreams into reality.

Why should I purchase my Winchester vacation package via Travelocity?

You'll not only enjoy big savings, but you'll also have access to our 24/7 support, high-quality service and a Price Match Guarantee. Wander across the world, discover hidden sights and make lifelong memories — we'll take care of the important details.

Can I save on my Winchester car rental if I bundle it with hotels and flights?

Combining your hotel, flight and car into a Winchester vacation package is the easiest way to land the best deal. Plus, having your own rental car gives you freedom to get to all those famous sights you want to see. Sitting 40 mi away from Winchester, Plymouth Rock is one attraction that should be on your itinerary. Buckle up and make a day trip of it.

Which airport is best for Winchester?

Many people fly into Logan Intl. Airport (BOS), 9 mi southeast of downtown Winchester. Others prefer T.F. Green Airport (PVD) (55 mi away from central Winchester) or Manchester-Boston Regional Airport (MHT) (35 mi away from central Winchester).

What is there to do in Winchester?

Snap up the excellent photo-ops at Winter Pond, one of the most well-known attractions in Winchester. There's plenty more to uncover in this exciting destination, so give yourself enough time to visit some of its hidden gems.

Where should I stay when visiting Winchester?

Many people spend their nights at the Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93. It's sure to be a good base for your Winchester getaway.